It was about halfway up App Gap, weaving on the 18% tarmac, with the front group rapidly retreating into the distance that I realised I probably shouldn’t have made GMSR my first race.

Let’s walk it back. A couple of months ago, I decided that enough was enough and that it was time to finally act like a racer by, you know, doing a race. But starting in a Central Park race didn’t quite scratch my itch–– if I was going to do my first race, I wanted to make it a good one. And that’s how, on a bright day sometime in mid-July, I ended up registering for the Green Mountain Stage Race, a four-day event in central Vermont that attracts teams from across the eastern seaboard. And I was going to race that, as my first race. The following is a listcal of sorts to guide you through every single one of the *numerous* mistakes I made in the process, and how you can avoid making them yourself.

Mistake 1: Don’t make GMSR your first ever race. An obvious one to start with. Do a race beforehand, any race, doesn’t matter which one. Just do it.

Before we dive in, here’s a quick bit of background and a rundown of how GMSR was structured this year for the 4/5 men:

• Day 1: 5.5-mile TT. One mile uphill, 4.5 miles rolling downhill. The whole thing takes somewhere between 15 to 20 minutes.

• Day 2: 35-mile circuit race. This is your classic park-style 35-miler on open roads. There’s a sprint and a KOM. As you’ll see in mistake number 5, it’s not really hard enough to drop anyone on this course.

• Day 3: 65-mile road race. Ah, day 3. Day 3 features 65 lumpy miles on open roads with a big lump in the middle, and an extremely steep lump at the end–– Appalachian Gap or ‘App Gap’ which tops out at 20% in the last km. There were probably sprints and KOMs on this stage but my soul left my body and I don’t remember anymore.

• Day 4: A 15 mile crit. 25 laps of a 0.6 mile circuit through central Burlington.

Day 1 went well for me. I came second in the TT by a single second. No real mistakes to speak of there. Unless you count not winning. Maybe that’s a mistake? Yeah, don’t come second by one second.

Mistake 2: Don’t lose in the TT. There isn’t much advice you can give in a TT, go fast and don’t lose.

Moving on to day 2. After a successful TT, I’m sitting second on GC by one second. Outwardly, things have gone well. Except, now I have to defend GC in my first ever circuit race... on my first ever road stage… of my first ever stage race. Thankfully I had a one-mile neutral roll-out to learn how to ride in a peloton. 

Mistake 3: Don’t make GMSR your first ever race. Worth reiterating. If I had done a race before, I’d know how to, say, ride in a pack.

The flag dropped outside of town and we were on action stations. Immediately, attacks started flying. One guy was apparently just doing shuttle runs up from the back, realising he didn't want to sit on the front and then immediately falling back. It was a surge-y and cagey and, sitting in second, I felt like I had to stick near the front and help keep things stitched together.

Mistake 4: You don’t need to do half as much as you think you do. Don’t go near the front, and just relax, it’s going to be fine.

About 10 miles in, one rider rode over a cone and took out half the field. I don’t know why there was a cone in the course and I don't know why nobody called it out. Nevertheless, the cone was there. 

Here’s the scene: we’re cruising along at 25-30 miles an hour when suddenly there’s a loud BANG. I look immediately to my right and see a bike cartwheeling through the air. A water bottle skitters across the road surface and into the wheel of a guy to my left who crashes. “I’m going to crash now. This is how I crash.” 

Somehow, me and a couple of others managed to sneak between the two guys who went down along with a few others. I look up to see the sprint trains and the yellow jersey disappearing up ahead and launch into a full sprint to catch back on. This was mistake number 5.

Mistake 5: I didn’t need to do that. This is sort of a sub-point to the previous mistake but yeah, things would have come back together naturally here. Something I would have known if GMSR wasn’t. my. first. race.

The next ten or so miles were uneventful. I ate a bar, we called out potholes, that one guy continued to do laps of the length of the group.

Then we hit the only climb of the day, a small bump of around 600 feet that comes at around 25 miles. I had Google-map-reconned the climb beforehand and had determined it would make the perfect platform to launch an attack.

Mistake 6: If an attack is going to stick, it has to be a really hard attack. GMSR is a tough field in any category, the guys I was racing against were not going to get dropped on this climb.

I hit the front exactly where I had planned to, I gave it everything, and turned around to see… the entire front group looking back at me completely unphased. Chastened, I fell back in and waited for the KOM which, bleeding through my eyeballs from my “attack”, I could not compete for.

Mistake 7: Wait for the KOM sprint. This is the beginning of what becomes a bit of a theme in my race, if you’re going to race for GC, wait for the last bit. 

The final miles unfolded rapidly but uneventfully. The finish sprang up on us and I sprinted for 7th without losing any time on GC. I had survived my first ever road stage of a bike race. Things were good. For now.

The first 30 miles of day 3 were boring so I’m skipping them. There was a four-mile neutral descent during which everyone froze, there was a sprint, everybody was on-edge after the previous day’s crash so no one attacked.

Then we hit the first climb –– Mid Gap–– and things started to heat up. The field strung out and before we knew it there were seven of us at the front taking chunks out of each other as we grappled with the gradient. I came over the KOM last of the seven guys but caught them on the descent. 

After a quick survey, we decided that this was a strong group of seven and that we should work together to maintain the gap we had created. Then everyone promptly failed to work together.

As we hared down the hill, I noticed that I kept opening space to the guys behind me and would have to continually tap the brakes to let them get back on. When this happened a third time I decided I was done waiting for them. Seeing this, one of the guys bridged the gap up to me and the break was on with 25 miles to go.

Mistake 8:* Breaking away with 25 miles left. I’m asteriscing this one because I actually stand by it. I knew I was not the strongest climber in the race by now so my options were either to wait for the final climb and get dropped, or gamble on getting to the final climb with a gap. 

For the next few miles, me and the fella in the U of Michigan jersey rolled turns. This was actually one of the highlights of the race for me–– real racing, trying to keep the peloton away. Soon though, my man’s turns started to slow so I apologized and went on ahead. “Sorry man, I gotta go.” “Go for it.” And so I was alone. Just me and the moto with its “Force B with U” sign taped to the back.

A couple of miles out of Bristol, the front group reeled me in again. The yellow jersey’s domestique who had been doing the chasing laughed and called me a motherfucker so I pretended to attack again.

The pace slowed as we entered the town and a few more guys joined the back. 

Then, as we were leaving the town and I was on the front again, I noticed a tiny gap had opened up between me and the group. Only ten feet or so. I looked at the yellow jersey and he didn’t close it. So I opened up another ten feet. Still nothing. 

Mistake 9: Going for a second breakaway with 10 miles and two categorized climbs still to go. Explains itself, really.

If you’ve raced before, as I had not, you probably know how this one goes. I got to the base of Baby Gap, and made it about 500 feet up the road before realising I had made a terrible mistake. Looking around, I saw the group close behind me now, maybe 20-10 seconds, so I held up and waited as I was quickly reincorporated.

Somehow, miraculously, I made it to the top of Baby Gap in that group but I was hurting badly. A quick rolling descent and we were into the main event–– App Gap. 2 miles to go. Everyone wished each other luck and that was that.

I think I made it around two corners before the guy in third place on GC switched it on and took off. I was immediately shelled, like instantly. It was chaos, some guys went with him but the group was shedding guys like a cheap pillow shedding feathers. After that, it was just a question of getting to the top. Weaving up the 18% grade, I dreamed of putting my foot down but knew that the relief would be far outweighed by having to clip in again. Here and there, I passed guys from the group ahead, but mostly I was the one getting passed.

Depleted, I rolled in 20th. I was 4:30 down on the winner and I was completely out of the GC (down to 15th), but I couldn’t have been happier. It’s an emotional thing to finish such a massive stage surrounded by friends and family. On to day 4.

I’ll tee this bad boy up by saying that I almost pulled out of the crit the night before. To me, I had made it through three days of racing, I’d had a great time, both me and my bike were intact, besides I had fallen out of GC contention, why risk it for a crit when I’m not even a sprinter? But, as someone gently pointed out to me, “this is part of the race that you paid to do” and a DNS in my first ever race didn’t sit right with me.

So it was that I found myself lining up for the final stage of GMSR in what would be my first crit. With Cullen’s advice ringing in my ears, “crits are a race to the start” (s/o Cullen) I squirmed my way to the front row of the start group.

We had a quick neutral lap, which I spent quietly jostling for position, then the flag dropped and the race was on. 

Over the course of the first three laps I was slowly worked into the back third of the pack. Realising this was not good, I decided to make a few big investments to get up to the front. The course in Burlington is not ideal for moving up, not many long straights and a few technical sections but I managed to get myself closer to the pointy end. 

Then, before I knew it, I was on the front. Too sketched-out to look behind, I pressed on. 

“We have a gap, go, go!” I heard from behind. 

Flying through a corner, I looked back to see that me and a guy from District Taco had opened up a tiny gap on the peloton, maybe five seconds. I was pretty gassed from the day before but beggars can’t be choosers so I pinned back my ears and gave him a turn.

Mistake 10: Doing a third breakaway in two days. 

Pls stop.

For the next ten laps we worked together in silence, we had one incoherent conversation about who should take sprint points (we agreed neither of us cared) and that was about it. Gradually though, the gap stopped growing and I could feel myself losing steam. Shortly after that, the pack was on us and we were reabsorbed. 

As the group came past, I knew my only hope was to hang on to the front three wheels, recover as much as possible and then go for the sprint. I worked my way  onto the wheel of the guy in second on GC and decided I wasn’t going to take a pull for anything. 6 laps to go.

As we turned into the final two laps, on the “dark side” of the course, the yellow jersey pulled up alongside me. “Get on my wheel, let’s GO”. I still don’t really get why he did this but I didn’t need to be asked twice, I hopped over and he hauled ass through the bend. Now, I was still second wheel but we were really cooking. 2 laps to go.

I kept expecting the sprint teams to start swarming but still no one came. We hit the final lap and I was still on this dude’s wheel with no one coming past me. ‘There’s no way the sprinters are going to be allowed to go through the last bend in second wheel.’ 3 corners to go. 2 corners to go. We’re on the penultimate straight. I’ve already picked my line through the last corner: over the lip of a drainage cover that acts like tiny banking and bounces you into the final straight like a ping pong ball. 

“GO” I yelled to my yellow leadout.

He peeled off and launched his sprint, I came past him and immediately I could hear the buzz of carbon wheels getting closer–– two actual sprinters who launched after me came through doing a good 200 W more than what I was doing, but I was still in third… and still in third… and still.

I came in a bike-length behind the two sprinters who threw for it–– I was probably the only person to ever post up for a third place, more from the emotion than anything else. 

And just like that the race was done. I hugged my teammates, and my wife. I had survived my first crit, my first road race, my first stage race, my first race! 

12th on GC, 2 podiums, 4th on the sprint classification (??) and I made 10 mistakes along the way but I did not make the mistake of letting the race pass me by.

Yes, you can do less work, you can wait for the final climb on stage 3, you can sit tight and spring a sprint for the KOM... But this is a race–– your first race, you should race it. That’s the beauty of doing GMSR as your first ever event, you can show up and make 10 terrible mistakes on the biggest amateur stage there is and show up next year and fix them. That’s what your second race is for. After all, you only get to race your first race once. Might as well make it a good one.